When Loudon Wainwright III released his first album in 1970, the music press branded him, as it had other young singer-songwriters, "The New Bob Dylan." Two decades later, in "Talking New Bob Dylan," a 1992 tribute to the rock and folk legend, Wainwright suggested that he and the other New Bob Dylans, "your dumb-ass kid brothers," get together at singer and songwriter Bruce Springsteen's house as part of a 12-step program. Wainwright has also been dubbed "the Woody Allen of Folk" and "the Charlie Chaplin of Rock."

Though originally lumped with the many singer-songwriters of the early 1970s, Wainwright's finely tuned wit served to separate him from the pack, and critics eventually stopped looking for comparisons. "[There are] a million amateurs out there who call themselves songwriters, but for my money, [there are] only a few who belong in this guy's league," asserted City Pages contributor Jim Walsh. Called "the not-so-sensitive folk singer" by Greg Reibman in Billboard, Wainwright built a cult following with funny, biting, and incisive songs about virtually any subject. He is, according to Tom Surowicz of the Twin Cities Reader, "a thoroughly compelling master of irony" and in Rolling Stone contributor David Browne's words, "our greatest pop satirist."

Wainwright was born in Chapel Hill, North Carolina, in 1946, but grew up in affluent Westchester County, New York, the eldest of the four children of renowned Life magazine editor and columnist Loudon Wainwright, Jr. His high school years were spent in Delaware, at the St. Andrews School for Boys, where he began to listen to and play folk music. Wainwright learned to play the guitar in his early teens and performed with a few folk groups at school. He also spent weekends at folk clubs in Philadelphia and saw Bob Dylan "go electric" at the Newport Folk Festival in 1965. Dylan was a big influence musically, as was folksinger and guitarist Ramblin' Jack Elliot. Wainwright went to Carnegie Mellon University in Pittsburgh to study acting and directing but left after a year and a half, dropping out in January of 1967 to head for San Francisco.

But by 1968, Wainwright was back East, living in Cambridge, Massachusetts. He started writing songs and playing in Boston-area, and occasionally New York City, clubs. It was at New York's Village Gaslight that Milton Kramer, a music publisher, caught Wainwright's act. Kramer quickly became his manager and secured him a recording contract with Atlantic Records in 1969. Wasting little time, Atlantic released Wainwright's first album, Loudon Wainwright III, in 1970, followed by Album II in 1971.

Wainwright's early work was personal and confessional, and the instrumentation was very spare--usually just the singer and his acoustic guitar. Critics were impressed. Reviewing the first album for Rolling Stone, Gary Von Tersch marveled, "Usually artists of Wainwright's obvious genius write and play out their lives and songs on old friends' back porches, in local smoke-stung coffeehouses or on anonymous sidewalks and park benches. Somehow Wainwright found his way onto a record. I just hope it's not a one-shot affair--he's got something to say." Though Stephen Holden, also of Rolling Stone, deemed the artist's first two offerings poorly produced, he acknowledged that "the records were wonderful. The crudeness of production, the extremely static nature of the music itself: these at least accentuated the poetry by making it inescapable." Also evident on the early albums was a bitterness that put some listeners off. Looking back a decade later, Steven X. Rea of High Fidelity recalled that these first attempts "were not easy records to listen to. The singer-songwriter ... was certainly clever and cunning, smart and satirical, but the emotions behind his words--sung in a high, bitter whine--were angry, distraught, and dark."

Wainwright's relationship with Atlantic was stormy and the label dropped him after Album II. Picked up by CBS Records, he released Album III in 1972. This LP was not only a critical success, but a popular one as well, reaching the Top 100. Much of the attention it garnered could be attributed to the comic song "Dead Skunk," which landed in the Top 20. Album III' s humor, in fact, marked a change in Wainwright's music. As he explained in Sing Out!, though he started his career as a fairly serious songwriter, "humor started to leak in after a couple of years, and rather than change what I was doing, I sort of threw gasoline on it, 'cause I enjoyed having people laugh at me--or with me." He told Craig Harris, author of The New Folk Music, that he also liked the way his new approach increased record sales, as did CBS, which pushed him to write more funny, commercial songs.

Wainwright released five more albums during the '70s, all of them sounding very commercial, according to High Fidelity' s Rea. But the singer was not particularly pleased with his work, even though his core of devotees continued to grow. Songs intended to ensnare a wide audience were not his forte. "Generally my impulse to write has been autobiographical. I never really thought much about writing something for the radio audience at large," he told Sing Out! "When I've half-heartedly tried to make radio records, they were failures." By 1976, CBS had dropped him and he had moved to Arista. Rolling Stone' s David Wild called Wainwright's Arista albums his "least distinguished efforts." Wainwright himself called them his "plane-crash albums." As he explained to the journalist, "When my plane goes down, those records come out again. At that time I was under pressure to have a hit single ... and I didn't know what the hell I was doing. I was just looking over my shoulder--completely freaked."

Wainwright had also spent the 1970s pursuing his interest in acting. He appeared in three episodes of television's M*A*S*H in 1975 and performed Off Broadway in the musical Pump Boys and Dinettes. This occupation continued into the '80s, when he appeared in two films-- The Slugger's Wife in 1985 and Jacknife in 1989--and on stage and television in Britain. Also during the '70s, Wainwright married singer Kate McGarrigle of the Canadian folk duo the McGarrigle Sisters, and the couple had two children, Rufus and Martha. But the marriage ended in 1977 and a year later, Arista let him go. "I just wound up at the end of the 70's in a heap," he confessed to Bill Flanagan in Musician. He left his manager and his agent, moved to California, and then to England. Except for a live LP released by Radar Records in 1979, Wainwright, who had dutifully unveiled an album every year since 1970, did not produce another until 1982.

In 1980 Wainwright started over, signing with independent record companies--Demon in England and Rounder in the U.S. As he told Flanagan in 1989, he loved the freedom of working with independents, which allowed him to make the music he wanted without the pressure to produce hit singles and big sales. "And slowly, through this decade I've made five albums just trying to somehow figure out how to do work that I feel good about that is related to something real." He began working with British folk and guitar favorite Richard Thompson, who played on his albums and helped produce several, and found a new manager in his sister Teddy. He married Suzzy Roche of the singing sister trio The Roches, and they had a daughter, Lucy, in 1982. The marriage to Roche didn't last either, but it apparently gave Wainwright plenty of new song material.

In this second phase of his career, Wainwright returned to more personal songwriting. As he mused in "Harry's Wall," from 1988's Therapy, "I guess by now you've noticed/ Almost all the songs I write/ Somehow pertain to me." Wainwright also, according to Rea, exhibited a "newfound emotional maturity." Reviewing 1982's Fame and Wealth, he asserted, "His first collection of new songs in four years shows a wiser, worldlier set of perceptions." The next album, 1985's I'm Alright, was co-produced by Thompson, who, according to High Fidelity' s Leslie Berman, encouraged Wainwright to concentrate on his "softer side." In doing so, he "[fashioned] a portrait of the artist as a gloomy hopeful fellow; the anger and disdain of so many of his earlier songs is gone. By toning down his negativity, he has discovered a more complicated and effective level of humor." I'm Alright was nominated for a Grammy Award for best contemporary folk recording, as was the 1986 follow-up, More Love Songs.

1988 saw Wainwright inching his way back to the major labels; that year's Therapy was recorded by Silvertone, another independent, but distributed by RCA. People' s David Hiltbrand considered Therapy an "uneven effort for Wainwright," but Rolling Stone contributor Wild felt differently, declaring, "? Therapy ? reaffirms that [Wainwright] is one of the wittiest and most literate singer-songwriters on the scene." Wainwright's following remained strong in the United States and England, which had become his primary residence. In 1989, England's Edsel Records reissued his first five albums.

Wainwright's faithful were rewarded in 1992 with History. Released by Virgin Records, it marked the artist's full return to the majors. Kent Zimmerman of the Gavin Report described History as "beautifully played, produced, sung and phrased," and along with the Twin Cities Reader' s Surowicz and Entertainment Weekly, assessed it as one of the best albums of the year. The family-focused record was highly personal--in the words of Wild, an "intimate, painfully honest album, which should be called Songs for the Whole Dysfunctional Family. " Less cynically, Dave DiMartino of Musician labeled History "Wainwright's shining moment of personal introspection."

Throughout his checkered recording career, Wainwright's mainstay has been his live performances--as he acknowledged to Musician' s Flanagan, saying, "I still more than anything love to play for people." Although High Fidelity contributor Berman judged his performances "mannered and predictable," Surowicz identified in Wainwright "a rare honesty, biting wit, moving depth, impish sex appeal, a punk's energy, a star actor's charisma, and a great biographer's gift for detail." His relationship with his audience is at once antagonistic and naked. As Flanagan described, onstage Wainwright is a "hammy extrovert, making faces as he sings, lifting one leg in the air, sticking out his tongue and then--unexpectedly--opening his veins for the audience's inspection."

In spite of his critical acclaim, Wainwright continued to feel the pinch of life on the musical fringe. "It would be bullshitting you to say that I don't want to be more successful. I'm obsessed with success and failure.... And I'm frustrated because I'm on the periphery of the music business," he admitted to Flanagan. In songs like "Harry's Wall" he takes stabs at his minor celebrity, and in "The Home Stretch," from More Love Songs, he rails, "But keep lifting your left leg/ And sticking out your tongue/ There's nothing else that you can do/ And you're too old to die young." Still, he conceded to Flanagan that he loves his job. "I'm one of those people who got to do basically what they wanted to do and get paid for it. So I consider myself very fortunate." Four years later, in the liner notes to his much-applauded 1993 live album Career Moves, he maintained his optimism, reporting, "In February of this year I did a show at the Royal Festival Hall in London and a few weeks later I was in Orlando, Florida, playing in a blues bar called the Junkyard. Both were good nights."

Through exposure on such venues as National Public Radio and the word of mouth of loyal fans and critics, Wainwright's satire, wit, and sincerity persisted in gracing both concert halls and bars. City Pages contributor Walsh suggested why: "Loudon Wainwright III leaves you with something. Something peculiar, something special, something to chew on. And though he says he draws lines as to how much he's willing to reveal about his life, he also writes with an unflinching honesty while others in his same arena cover up with poetry and volume." Wainwright countered, "Well, it could just be my exhibitionist tendencies, too; I don't think we have to turn it into so much of a noble thing." This characteristic deflation only confirmed Holden's New York Times explanation of Wainwright's appeal. "A great singing storyteller," the music scribe ventured, "he still projects the slightly scary radarlike vision of a precocious brat who sees through all disguises, including his own, and feels compelled to tattle on everybody."

by Megan Rubiner Zinn

Loudon Wainwright, III's Career

Began writing and performing in Boston and New York City, 1968; signed with Atlantic Records, 1969, and released Loudon Wainwright III, 1970; signed with CBS Records, and released Album III, 1972; signed with Arista Records, c. 1976; signed with Demon Records in England, Rounder in the U.S., and released Fame and Wealth, 1982; appeared in films The Slugger's Wife, 1985, and Jacknife, 1989; performed on stage and television in England, 1980s--.

Loudon Wainwright, III's Awards

Grammy award nominations for best contemporary folk recording, 1986, for I'm Alright, and 1987, for More Love Songs.